Carbon Dioxide → HCID 18509451, compound

HRID 1356834Notes

Reaction equation

HRID 1356834 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:22](=O)=[O:23].C([Li])CCC.CCCCCC.CN(C)C=O.[Cl-].[NH4+]>O1CCCC1.CC(C)=O>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH:22]=[O:23])[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 18509495HCID 18509495, compoundHCID 178418339Butyllithium

Product 1

HCID 18509451HCID 18509451, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 78 (2.26 g; 6.53 mmol) was dissolved in tetrahydrofuran (25 ml), and the solution was cooled to −75° C. by use of a mixture of dry ice and acetone solvent under nitrogen atmosphere. n-butyl lithium in n-hexane (1.56 M: 4.2 ml; 6.53 mmol) was slowly added dropwise to the mixture, and the resultant mixture was stirred for 15 minutes. Subsequently, N,N-dimethylformamide (0.95 g; 13.1 mmol) was added dropwise to the mixture, and the resultant mixture was gradually brought to room temperature. Reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with ether (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.59 g of the target compound (yield: 30.6%).

Workup

  1. customwas gradually brought to room temperature
  2. customReaction
  3. extractionfollowed by extraction with ether (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2264196a446d4caf893272ea04777c4c
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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